That's a good point about the transaction history. Do you know if the CSV export includes cost basis information? And regarding crypto, have you found any good solutions for tracking those transactions from Robinhood?

The CSV export does include the purchase price for stocks and options, which gives you the cost basis information. However, it doesn't automatically calculate adjusted basis for wash sales - you'd need to do that yourself or use tax software. For crypto tracking from Robinhood, I've found CoinTracker works pretty well. You can't directly connect it to Robinhood automatically, but you can import the transaction CSV from Robinhood into CoinTracker. It takes a bit of manual work upfront, but then gives you much better crypto tax reporting than what Robinhood provides. Koinly is another option some friends have used successfully with Robinhood exports.

Not my experience at all. Last year, Robinhood sent corrected 1099s THREE TIMES, with the final one coming in early April. Totally messed up my filing timeline. Apparently it's pretty common with them if you have wash sales or more complex situations.

Thank you, I hadn't even thought about all those other tax benefits that would be affected. We do have some student loan interest and education credits that would be impacted. Looks like filing jointly and taking the premium tax credit hit is even more clearly the right move than I initially thought.

Happy to help! Yeah, the MFS status really limits a lot of tax benefits, which is why it's rarely the optimal choice unless there are very specific circumstances. The premium tax credit "marriage penalty" is frustrating, but thankfully it's just a one-time adjustment you're dealing with. Next year you'll be able to plan your insurance coverage for the full year as a married couple and avoid this issue completely.

This is really smart. I did this exact thing last year. Was going to owe $2,400 in premium tax credits after getting married, but maxed out my HSA ($3,850) and put another $2,000 in my traditional IRA. Dropped our MAGI just enough to reduce the repayment to only $800. Definitely worth looking into!

I hadn't thought about this angle! We do have some room to make additional retirement contributions. I'll need to check exactly how close we are to the next MAGI threshold for the premium tax credits. Even if it just reduces the amount a bit, that's still a win since we'd be putting money into our retirement rather than just paying it to the IRS. Thanks for the suggestion!

Can you explain more about how to document this? Like what kind of proof would you need to show the IRS that your education is "ordinary and necessary" for your business? I'm taking some digital marketing courses and want to deduct them for my Etsy shop.

Documentation is crucial. I keep a business education folder with: course descriptions/syllabi highlighting specific skills taught, a written explanation connecting each course to specific aspects of my current business operations, evidence that these skills are industry standards (like professional association recommendations), and a log tracking how I've implemented these skills in my business. For your digital marketing courses and Etsy shop, save the course descriptions, then create a document explaining how each marketing technique directly applies to growing your existing Etsy business. Track your marketing metrics before and after implementing what you learn to show business purpose. If similar businesses commonly use these marketing techniques, note that as evidence that the education is "ordinary" in your field.

That's a really good point about credits vs deductions! I think business expense deductions don't have the same caps as education credits though? At least that was my understanding. Can you take BOTH the business education deduction AND education credits for the same expenses?

Would I have to pay taxes on the conversion from after-tax to Roth though? I'm confused about how this is different from just doing a backdoor Roth IRA.

You only pay taxes on the growth between the time you make the after-tax contribution and when you convert it to Roth. If you convert frequently (some plans even allow automatic conversions), this tax amount is minimal. The main difference from a backdoor Roth IRA is the amount you can contribute. A backdoor Roth IRA is limited to $7,000 per year (2025 limit for those under 50). With the mega backdoor Roth, you could potentially contribute up to around $43,500 more (the exact amount depends on your plan and the total annual 401k limit of $70,000 for 2025 minus your regular contributions and employer match).

Great point about the flexibility! But don't you lose a lot to taxes on dividends and capital gains compared to Roth growth that's completely tax-free?

Thanks for the recommendation! I've heard good things about TaxAct from a coworker too. Did you find their interface easy to use? I'm not super tax-savvy and need something that explains things clearly.

Their interface is pretty straightforward and they explain tax concepts in plain English. They use a question-based approach that helps catch things like HSA contributions without you needing to know which specific forms are required. The help sections are quite clear with examples, and if you get stuck, they have decent customer support through chat. For someone who isn't tax-savvy, they offer good guidance without overwhelming you with jargon. Their review system also catches common errors before you file.

FreeTaxUSA is such an underrated option. Been using them for 4 years now and they handle everything correctly including my rental property and side business. None of the upselling garbage that TurboTax does either.